4,4'-dibromostilbene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,4'-dibromostilbene
• 英文别名: 4,4'-Dibrom-stilben；1,2-bis(4-bromophenyl)ethene；1,2-bis(4-bromophenyl)ethylene；1-broMo-4-[2-(4-broMophenyl)ethenyl]benzene
• 化学式: C₁₄H₁₀Br₂
• 分子量: 338.041
• InChiKey: JEHMPNUQSJNJDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4,4'-dibromostilbene 在 Oxone 作用下， 以 水 、 乙腈 为溶剂， 反应 22.0h， 以83%的产率得到4-溴苯甲酸
  参考文献：
  名称：

  Oxidation cascade with oxone: cleavage of olefins to carboxylic acids

  摘要：

  A variety of olefins is shown to be cleaved oxidatively to the corresponding acids with oxone as the reagent. The simple methodology that works well for a range of alkenes, i.e., styrenes, nitrostyrenes, stilbenes, cinnamic acids, chalcones, etc., involves heating of the reactant with oxone in acetonitrile-water mixture (1:1, v/v) at reflux. The oxidation cascade involves initial dihydroxylation followed by oxidative cleavage and oxidation of the resultant aldehydes to acids. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.01.042
• 作为产物：
  描述：

  bis-(4-bromo-benzylidene)-hydrazine 生成 4,4'-dibromostilbene
  参考文献：
  名称：

  Buu-Hoi,N.P.; Saint-Ruf,G., Bulletin de la Societe Chimique de France, 1968, p. 2489 - 2492

  摘要：

  DOI：

文献信息

• Studies in photochemistry. Part VII. The photocyclisation of some nuclear-substituted stilbenes to substituted phenanthrenes
  作者：E. V. Blackburn、C. E. Loader、C. J. Timmons

  DOI：10.1039/j39680001576

  日期：——

  Photocyclodehydrogenation of trans-9-styryl-1,2,3,4,5,6,7,8-octahydroanthracene in cyclohexane solution formed a mixture of 11-butyl- and 11-but-3-enyl-1,2,3,4-tetrahydrochrysene in very small yield, identified by their i.r., u.v., 1H n.m.r., and mass spectra. 2,4,6-Trimethylstilbene photocyclised to 1,3-dimethylphenanthrene with the elimination of a methyl group. 3,3′,5,5′-Tetramethylstilbene formed

  在环己烷溶液中反式-9-苯乙烯基-1,2,3,4,5,6,7,8-八氢蒽的光环脱氢反应形成11-丁基-和11-丁-3-烯基-1,2,3的混合物通过其ir，uv，1 H nmr和质谱鉴定的1,4-四氢丙烯收率非常低。2,4,6-三甲基sti光环化为1,3-二甲基菲并消除了甲基。当在环己烷溶液中照射时，3,3'，5,5'-四甲基sti形成了2,4,5,7-四甲基菲。类似地，4，4′-二溴-和4，4′-二氰基-sti形成相应的3，6-二取代的菲。
• Electrochemical Aziridination by Alkene Activation Using a Sulfamate as the Nitrogen Source
  作者：Jin Li、Wenhao Huang、Jingzhi Chen、Lingfeng He、Xu Cheng、Guigen Li

  DOI：10.1002/anie.201801106

  日期：2018.5.14

  direct aziridination of triaryl‐substituted alkenes was achieved by means of an electrochemical process that could extend to multisubstituted styrenes. Specifically, hexafluoroisopropanol sulfamate was used as a nucleophilic nitrogen source. Mechanistic experiments suggest that this electrochemical process proceeds by stepwise formation of two C−N bonds through reactions between cationic carbon species

  三芳基取代的烯烃的第一次直接叠氮化是通过电化学方法实现的，该方法可以扩展到多取代的苯乙烯。具体而言，将六氟异丙醇氨基磺酸盐用作亲核氮源。机理实验表明，该电化学过程是通过阳离子碳物质与氨基磺酸盐之间的反应逐步形成两个C-N键而进行的。
• B( <scp> C ₆ F ₅ </scp> ) <scp> ₃ ‐Catalyzed </scp> Hydroboration of Alkenes with <scp> <i>N</i> ‐Heterocyclic </scp> Carbene Boranes <i>via</i> B—H Bond Activation
  作者：Qiaotian Wang、Wei Meng、Xiangqing Feng、Haifeng Du

  DOI：10.1002/cjoc.202000489

  日期：2021.4

  Significantly, excellent regioselectivities were obtained in some cases. Mechanistic studies indicate that the B—H bond cleavage is likely involved in the rate‐determining step. In addition, an electrophilic addition of NHC‐borenium cation to alkenes and the subsequent formation of carbocation are also postulated. The current work provides a promising method for the activation of stable borane adducts

  在这项工作中，开发了一种新的活化N-杂环卡宾硼烷（NHC-硼烷）的方式，该方式是通过以沮丧的Lewis对方式通过路易斯酸B（C 6 F 5）3氢化物提取生成高反应性的两性离子物质。B（C 6 F 5）3的合适底物包括苯乙烯，β-甲基苯乙烯，苯乙烯和烷基烯烃等多种烯烃。催化硼氢化以高至高收率提供所需的产品。显着地，在某些情况下获得了优异的区域选择性。机理研究表明，在确定速率的步骤中可能涉及到B键的断裂。此外，还假定将NHC-硼阳离子亲电加成到烯烃中，并随后形成碳正离子。目前的工作为稳定硼烷加合物的活化提供了一种有前途的方法，这可能在将来引起一些有趣的转变。
• Synthesis of <i>C</i> ‐ and <i>N</i> ‐Substituted 1,5,2,6‐Dithiadiazocanes –Electrophilic‐Nucleophilic Thioamination (ENTA) Reagents
  作者：Tomas Javorskis、Arminas Jurys、Gintautas Bagdžiūnas、Edvinas Orentas

  DOI：10.1002/adsc.202100424

  日期：2021.7

  A synthetic method is presented for S−N bond formation starting from cheap and affordable materials. We show that (un)substituted N-protected cyclic eight-membered C2-symmetric sulfenamides have been prepared in a few steps using this procedure. The synthetic utility of these ambipolar derivatives was demonstrated in a variety of synthetic transformations affording different S,N-heterocyles of pharmaceutical

  提出了一种从廉价且负担得起的材料开始形成 S-N 键的合成方法。我们表明，已使用此程序在几个步骤中制备了（未）取代的N保护的环状八元C 2对称次磺酰胺。这些双极性衍生物的合成效用已在各种合成转化中得到证明，这些合成转化可在一个或两个步骤中从简单的起始材料提供具有药物相关性的不同S,N-杂环。
• Cycloaddition Reactions of Alkene Radical Cations using Iron(III)‐Phenanthroline Complex
  作者：Yong Hyun Cho、Jae Hyung Kim、Hyeju An、Kwang‐Hyun Ahn、Eun Joo Kang

  DOI：10.1002/adsc.202000191

  日期：2020.5.26

  oxidation of electron‐rich alkenes using the iron(III)‐phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri‐ and tetra‐substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable

  使用铁（III）-菲咯啉配合物对富电子烯烃进行单电子氧化可产生亲电子烯烃自由基阳离子，从而促进了重氮化合物与自由基阳离子[2 + 1]的高效环加成反应。随后的链增长得到三和四取代的环丙烷。该方法还扩展到了与乙烯基重氮酯的[3 + 2]环加成反应，验证了这种可持续的第一行过渡金属铁系统的单电子氧化还原反应。